Dust-free pigment compositions obtainable by spray-drying

ABSTRACT

The invention relates to a composition comprising from 92 to 97% by weight pigment and from 3 to 8% by weight binder, in each case based on the composition, wherein the binder is a mixture comprising: from 5 to 60% by weight, based on the binder, of modified cellulose wherein, on average, per glucose unit, from 0.5 to 1.4 hydroxyl hydrogen atoms are replaced by R 1 , from 0.25 to 0.6 hydroxyl hydrogen atoms are replaced by R 2 , or from 0.5 to 1.4 hydroxyl hydrogen atoms are replaced by R 1 , and from 0 to 0.6 hydroxyl hydrogen atoms are replaced by R 2 ; and from 40 to 95% by weight, based on the binder, of a compound of formula (I) wherein Q is a hydrocarbon radical containing from 8 to 24 carbon atoms, unsubstituted or mono- to tri-substituted by hydroxy or OR 1 , each R 1 , independently of any other R 1 , is C 1 -C 4 alkyl or C 1 -C 4 alkylcarbonyl, each R 2 , independently of any other R 2 , is an organic group different from R 1  and containing from 2 to 10 carbon, from 0 to 4 oxygen and from 0 to 2 nitrogen atoms, and R 3  and R 4  are each independently of the other hydrogen, R 1 , R 2 , C 5 -C 8 alkyl, C 5 -C 8 alkylcarbonyl, C 5 -C 8 alkenyl, C 5 -C 8 alkenylcarbonyl, C 5 -C 8 cycloalkyl, C 5 -C 8 cycloalkylcarbonyl, C 5 -C 8 cycloalkenyl, C 5 -C 8 cycloalkenylcarbonyl, phenyl, benzoyl, tolyl, methylbenzoyl, benzyl, phenylacetyl, phenethyl or styryl. The compositions according to the invention are dust-free and produce outstanding colorations. The use thereof as colorants for, especially, polyolefins and the preparation thereof, especially by aqueous dispersal and spray-drying, are also claimed.

The demands made of pigment preparations are becoming ever greater. Thedevelopment of as little dust as possible during manipulation and alsogood colouristic results, which demand excellent dispersibility, areespecially important. The invention relates to pigment preparationsbased on a basically binary binder formulation of cellulose derivativesand fatty acid or fatty amine derivatives, which can be obtained in ahigh yield by very simple means by spray-drying and which exhibitexceptionally good results on application.

U.S. Pat. No. 5,455,288 discloses dustless pigment granules formed in amixer by means of fictional heat. Fatty acid esters and amides(especially erucamide), in a typical amount of from 2 to 20% by weight,are used as binders.

U.S. Pat. No. 4,264,552 discloses the production of a substantially dry,low-dusting and free-flowing granular pigment by spraying pigmentmaterial with water in a fluidised-bed apparatus. As binders there areused, inter alia, optionally ethoxylated fatty acid amines and amides inan amount of from 0.5 to 20% by weight. In Example 18, an amine mixturecomprising hydroxypropyl cellulose and unsaturated C₁₈ alcohol iscombined, the dust index being reduced from 78 to 30. In Example 19,abietyl-amine, hydroxyethyl cellulose and sodium alkyl naphthalenesulfonate are used together.

The properties of cellulose derivatives differ greatly depending on thetype of substitution and degree of substitution of the hydroxy groups.Commercially available hydroxyethyl celluloses having an average degreeof substitution (DS) of from 0.85 to 1.35 and a degree of molarsubstitution (MS) of from 1.5 to 3 and also commercially availablehydroxypropyl celluloses having a degree of molar substitution (MS) offrom 4 to 4.5 are known to be water-soluble whereas, for example, methylcellulose having a low degree of substitution is soluble only inalkaline media and methyl cellulose having a high degree of substitutionis soluble only in organic solvents.

Novel compositions have now been found which meet the highestcolouristic demands and which are very simple to produce. In addition,surprisingly, it is possible, by extremely simple means, to obtain thepigment compositions according to the invention in the form of dust-freegranules by spray-drying.

The invention accordingly relates to a composition comprising from 92 to97% by weight pigment and from 3 to 8% by weight binder, in each casebased on the composition, wherein the binder is a mixture comprising

-   -   from 5 to 60% by weight, based on the binder, of modified        cellulose wherein, on average, per glucose unit, from 0.5 to 1.4        hydroxyl hydrogen atoms are replaced by R₁, from 0.25 to 0.6        hydroxyl hydrogen atoms are replaced by R₂, or from 0.5 to 1.4        hydroxyl hydrogen atoms are replaced by R₁ and from 0 to 0.6        hydroxyl hydrogen atoms are replaced by R₂; and    -   from 40 to 95% by weight, based on the binder, of a compound of        formula

wherein Q is a hydrocarbon radical containing from 8 to 24 carbon atoms,unsubstituted or mono- to tri-substituted by hydroxy or OR₁,

each R₁, independently of any other R₁, is C₁-C₄alkyl orC₁-C₄alkylcarbonyl,

each R₂, independently of any other R₂, is an organic group differentfrom R₁ and containing from 2 to 10 carbon, from 0 to 4 oxygen and from0 to 2 nitrogen atoms,

and R₃ and R₄ are each independently of the other hydrogen, R₁, R₂,C₅-C₈alkyl, C₅-C₈alkylcarbonyl, C₅-C₈alkenyl, C₅-C₈alkenylcarbonyl,C₅-C₈cycloalkyl, C₅-C₈cycloalkylcarbonyl, C₅-C₈cycloalkenyl,C₅-C₈cycloalkenylcarbonyl, phenyl, benzoyl, tolyl, methylbenzoyl,benzyl, phenylacetyl, phenethyl or styryl.

The glucose units —[C₆H₁₀O₅]— in modified cellulose are usually in theform of glucopyranosyl, pairs of which form a cellobiose unit They may,however, also be in open hydrolysed form.

R₁ is preferably methyl or ethyl, especially methyl.

R₂ is preferably benzyl, C₁-C₄alkylene-COOR₃, C₂-C₃alkylene-NR₃R₄ or[C₂-C₃alkylene-O]₁₋₄—R₃, especially [C₂-C₃alkylene-O]₁₋₂—H.

When hydroxyl hydrogen atoms are replaced by both R₁ and R₂, then thetotal of hydroxyl hydrogen atoms replaced by R₁ and R₂ is preferablyabout from 0.6 to 1.5.

R₃ and/or R₄ are preferably hydrogen or R₂, especially hydrogen, veryespecially both simultaneously hydrogen.

Q may be linear, branched, cyclic (including polycyclic), saturated,mono-unsaturated, or conjugated or isolated polyunsaturated (e.g. di- ortri-unsaturated) and may also contain one or more (e.g. two) aromaticrings. Preferably, Q is saturated or monounsaturated and linear orbranched. A plurality of rings may be individual or fused, as in, forexample, terpenes, steroids or polyaromatic compounds. For high demands,the number of carbon atoms in Q may be related to the number of carbonatoms in R₃ as follows. Q preferably has at least 12 carbon atoms,especially when R₃ is hydrogen, C₁-C₄alkyl or C₁-C₄alkylcarbonyl.Special preference is given to Q being a hydrocarbon radical containingfrom 14 to 20 carbon atoms, especially a hydrocarbon radical containingfrom 16 to 18 carbon atoms, and to R₃ being hydrogen, methyl or ethyl,especially hydrogen.

The binder may optionally comprise as components from 0 to 20% by weightof any desired further substances, preferably organic or inorganic acidsor non-ionic compounds. Acids are, where applicable, contained in anamount such that, on dispersal of one part by weight of the compositionaccording to the invention in four parts by weight of water, thereresults a pH value of from 4 to 7, preferably from 4.5 to 6.5,especially from 5 to 6.

The acid is, for example, hydrochloric acid, sulfuric acid or an organicacid such as formic acid, acetic acid, propionic acid, lactic acid,oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid,maleic acid, fumaric acid, butyric acid, isobutyric acid, pivalic acid,benzoic acid, phenylacetic acid or phthalic acid.

Preferred organic acids have from 1 to 8 carbon atoms, especially from 1to 4 carbon atoms, and are unsubstituted or substituted by hydroxy.Special preference is given to formic acid and, especially, acetic acid.

However, apart from the acid, the amount of further components ispreferably as small as possible; special preference is given to therebeing no further component.

Pigments may be organic or inorganic and are, for example, from the1-amino-anthraquinone, anthanthrone, anthrapyrimidine, azo, azomethine,quinacridone, quinacridonequinone, quinophthalone, dioxazine,diketopyrrolopyrrole, flavanthrone, indanthrone, isoindoline,isoindolinone, isoviolanthrone, perinone, perylene, phthalocyanine,pyranthrone or thioindigo series, including those, where applicable, inthe form of metal complexes or lakes. Azos may be, for example, mono- ordis-azo pigments from any known sub-class, obtainable, for example, bycoupling, condensation or lake formation.

By way of example, examples of organic pigments include Colour indexPigment Yellow 3, 12, 13, 14, 17, 24, 34, 42, 53, 62, 74, 83, 93, 95,108, 109, 110, 111, 119, 123, 128, 129, 139, 147, 150, 164, 168, 173,174, 184, 188, 191, 191:1, 193, 199, Pigment Orange 5, 13, 16, 34, 40,43, 48, 49, 51, 61, 64, 71, 73, Pigment Red 2, 4, 5, 23, 48:1, 48:2,48:3, 48:4, 52:2, 53:1, 57, 57:1, 88, 89, 101, 104, 112, 122, 144, 146,149, 166, 168, 177, 178, 179, 181, 184, 190, 192, 194, 202, 204, 206,207, 209, 214, 216, 220, 221, 222, 224, 226, 254, 255, 262, 264, 270,272, Pigment Brown 23, 24, 33, 42, 43, 44, Pigment Violet 19, 23, 29,31, 37, 42, Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 28, 29,60, 64, 66, Pigment Green 7, 17, 36, 37, 50, Pigment White 6, PigmentBlack 7, 12, 27, 30, 31, 32, Vat Red 74,3,6-di(3′-cyano-phenyl)-2,5-dihydro-pyrrolo[3,4]pyrrole-1,4-dione or3-phenyl-6-(4-tert-butyl-phenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione.

Preference is given to azobenzimidazolone, disazo and polycyclicpigments and also to isoindolinones and diketopyrrolopyrroles.

Special preference is given to the pigment being a quinacridone,dioxazine, perylene, diketopyrrolopyrrole or disazo condensation pigmentQuinacridones are preferably prepared by oxidation ofdihydroquinacridones using hydrogen peroxide, as described, for example,in U.S. Pat. No. 5,840,901 or WO-02/077104.

The pigments may be single chemical compounds or mixtures of a pluralityof components, including solid solutions or mixed crystals containing aplurality of chemical compounds. Preference is given to uniformlycrystalline pigments as they usually yield greater colour saturationthan physical mixtures and mixed phases. If duller shades arenevertheless desired in the final application, this may be achieved bytoning down with colorants of different colour in a manner known per se.

The compositions according to the invention consist, preferably, only ofpigment and binder, especially of pigment, methyl cellulose, and acompound of formula

neutralised with approximately one equivalent of acid. They have aparticle size of preferably from 0.005 to 10 mm, especially from 0.05 to0.5 mm (that is to say, fine granules).

The compositions according to the invention can be used for anycustomary purpose, for example in the mass-colouring of polymers (or ascolorants for other organic materials of natural or synthetic originhaving a molecular weight usually in the range from 10³ to 10⁸ g/mol),including those in the form of fibres, surface-coating compositions(including special-effect finishes, including those for the automotivesector) and printing inks, or also in so-called resists or as toners.Such uses will be so obvious to the person skilled in the art that it ispossible to dispense with listing them here. They are also disclosed innumerous patent specifications and technical works, for example“Industrielle Organische Pigmente” (W. Herbst+K. Hunger, VCHWeinheim/New York, new editions continually published in German andEnglish).

The principal advantages are the very low dust formation, hightinctorial strength and colour saturation, outstanding dispersibility,excellent rheology, which allows use in high concentrations, and also ahigh degree of compatibility with a very wide range of substrates to bepigmented so that the range of pigments can be streamlined ineconomically advantageous manner. The compositions according to theinvention are moreover distinguished by good general properties, such asresistance to migration, to light and to weathering.

The pigment compositions according to the invention have proved to beespecially advantageous in isotactic, syndiotactic and atacticpolyolefins, especially in polybutadiene, polybutene, polyisobutene,poly(4-methyl-1-pentene), polyethylene, polypropylene, polystyrene andalso ethylene/propylene, styrene/acrylonitrile,acrylonitrile/butadiene/styrene and styrene/butadiene copolymers, e.g.PEC, PE-HD, PE-LD, PE-LLD, PE-MD, PE-UHM(W), PE-V, PEX, EPM, EPDM, ABSor EPS, and also in vinyl polymers including PVC, polyvinyl acetate,polyacrylates polymethacrylates and copolymers thereof, and alsocopolymers of polyolefins with, for example, polyethers, polyetherketones or polyurethanes.

The colouring of high molecular weight organic substances with thecompositions according to the invention is carried out, for example, byadmixing the compositions, where appropriate in the form ofmasterbatches, with the substrates using roll mills or mixing orgrinding apparatuses. The coloured material is then brought into thedesired final form using methods known per se, such as calendering,compression moulding, extrusion, coating, pouring or injection moulding.Where appropriate, known additives, for example dispersants, rheologyimprovers, film-formers, siccatives, plasticisers, fillers, reinforcingagents, antifoams and/or other additives, such as processing adjuvants,UV absorbers, luminescence quenchers, antioxidants, free radical captureagents (e.g. for ¹O₂) and/or other stabilisers, can also be added in anydesired amounts known per se. The additives can be incorporated in thepolymers before, at the same time as or after the compositions accordingto the invention. It is furthermore possible for the high molecularweight organic substances to be admixed with other colour-impartingconstituents, such as white, coloured, black or effect pigments in anydesired amounts, in addition to the composition according to theinvention, in order to obtain different hues.

Colouring is carried out preferably by mixing the pigment compositionaccording to the invention with the polyolefin granules or powder andprocessing the mixture into fibres, films or granules (including thosein the form of masterbatches). The latter can themselves then be, forexample, spun into fibres, calendered into sheets, extruded intoprofiles or formed into articles in an injection-moulding method.

The invention accordingly relates also to a method of pigmenting apolyolefin (including polystyrenes and vinyl polymers) or a polyolefincopolymer, wherein from 0.01 to 230% by weight, preferably from 0.05 to5% by weight, based on the polyolefin or polyolefin copolymer, of acomposition according to the invention is incorporated in a polyolefinor polyolefin copolymer.

The composition according to the invention is prepared by anyadvantageous method, but preferably in aqueous dispersion at a pH valueof from 4 to 7, preferably from 4.5 to 6.5, especially from 5 to 6. Tothat end the constituents of the composition according to the inventionand water are added in succession or simultaneously to an apparatuswherein by any suitable means the pigment particles are dispersed ashomogeneously as possible, after which the aqueous medium is removed bysuitable means. The amount of aqueous medium is advantageously from 1.5times to 100 times, preferably from 2.5 times to 10 times, especiallyfrom 3 times to 6 times, more especially from 3.5 times to 4.5 times,the dry pigment weight.

Advantageous aqueous media are water and also single-phase mixtures ofat least 30% by weight, preferably at least 80% by weight, water withinert, neutral liquids, for example customary hydrophilic solvents, suchas alcohols or ketones (especially methanol, ethanol, acetone or methylethyl ketone). When inert, neutral liquids are present, they preferablyhave a boiling point of from 50 to 120° C. or form, together with water,an azeotrope having a boiling point of from 50 to 120° C.

Known dispersing means are, for example, stirrers of any desiredgeometry and stirring speed, dispersers, homogenisers, nozzle mixers,drums, kneaders, screw apparatuses, shaking devices, vibrators orultrasonic devices. Known means of water removal, optionally after priorfiltration or centrifugation, are, for example, dryers or lyophilisationdevices, preferably spray dryers.

The invention accordingly relates also to a method of preparing acomposition according to the invention, wherein an aqueous medium, apigment, and a binder comprising

-   -   from 5 to 60% by weight, based on the binder, of modified        cellulose wherein, on average, per glucose unit, from 0.5 to 1.4        hydroxyl hydrogen atoms are replaced by R₁, from 0.25 to 0.6        hydroxyl hydrogen atoms are replaced by R₂, or from 0.6 to 1.4        hydroxyl hydrogen atoms are replaced by R₁ and from 0 to 0.6        hydroxyl hydrogen atoms are replaced by R₂; and    -   from 40 to 95% by weight, based on the binder, of a compound of        formula

-   -   and, optionally, from 0 to 20% by weight of further substances;        wherein Q is a hydrocarbon radical containing from 8 to 24        carbon atoms, unsubstituted or mono- to tri-substituted by        hydroxy or OR₁,

each R₁, independently of any other R₁, is C₁-C₄alkyl orC₁-C₄alkylcarbonyl,

each R₂, independently of any other R₂, is an organic group differentfrom R₁ and containing from 2 to 10 carbon, from 0 to 4 oxygen and from0 to 2 nitrogen atoms,

and R₃ and R₄ are each independently of the other hydrogen, R₁, R₂,C₅-C₈alkyl, C₅-C₈alkylcarbonyl, C₅-C₈alkenyl, C₅-C₈alkenylcarbonyl,C₅-C₈cycloalkyl, C₅-C₈cycloalkylcarbonyl, C₅-C₈cycloalkenyl,C₅-C₈cycloalkenylcarbonyl, phenyl, benzoyl, tolyl, methylbenzoyl,benzyl, phenylacetyl, phenethyl or styryl,

and wherein the weight ratio of pigment to binder is from 92:8 to 97:3and the weight ratio of pigment to aqueous medium is from 1:1.5 to1:100, preferably from 1:2.5 to 1:10,

are successively or simultaneously added to an apparatus which is sooperated that there results an aqueous dispersion having a pH value offrom 4 to 7, preferably from 4.5 to 6.5, especially from 5 to 6, and theaqueous medium is subsequently removed.

The pigment is preferably employed in the form of a moist pigment cakedirectly from synthesis or conditioning (e.g. recrystallisation or saltkneading). The aqueous medium is preferably removed by spray-drying,which surprisingly, when the weight ratio of pigment to binder is asstated above and the operating conditions of the spray dryer are ascustomarily used, produces unexpectedly good results in terms ofcolouristic properties, dispersibility and dust rating. As describedhereinbefore, in order to adjust the pH value, a small amount of acid isadded, if necessary, which usually remains as a constituent of thecompositions according to the invention on subsequent drying.

The addition sequence is, in itself, unimportant and is usually governedboth by the physical properties of the ingredients, especially theirviscosity, and by the apparatus available. It is possible, for example,first to stir together water and pigment presscake in a vessel, followedby addition (in the order stated) of a fatty amine, modified celluloseand acid, it also being possible to add the latter before the fattyamine or between the fatty amine and the modified cellulose.Alternatively it may prove advantageous first to introduce water intothe vessel, to incorporate the modified cellulose therein and then,after a readily stirrable homogeneous mass has been obtained, to add thefatty amine and acid (or, instead, the binary salt thereof and only atthe end to incorporate the pigment presscake in portions orcontinuously. However, the invention is in no way limited to thosesequences, which are mentioned solely by way of example, but ratherallows all kinds of alternatives, as the person skilled in the art willreadily recognise.

The aqueous medium may be removed completely or only in part, anyresidual moisture that remains being advantageously from 0 to 20% byweight, preferably from 0 to 5% by weight, especially from 0 to 2% byweight, based on the composition according to the invention.

The Examples that follow illustrate the invention without, however,limiting its scope (unless otherwise specified, “parts” or “%” arealways parts by weight or percent by weight, respectively):

EXAMPLE 1

756 parts by weight of 25% aqueous presscake of C.I. Pigment Red 144direct from synthesis are slurried with 9 parts by weight of tallowamine (Armeen TD™, Akzo Nobel), 1 part by weight of methyl cellulose(Metolose SM-100™, approximately 30% methoxy content, ShinEtsu) and 189parts by weight of water to form a suspension. The pH value is adjustedto 5.0 using hydrochloric acid and stirring is continued. In theprocess, the initially slimy viscous phase becomes a homogeneoussuspension which at 25° C. has a viscosity of about from 10 to 25 mPa·sat a shear rate of from 200 to 1000 sec⁻¹. The homogeneous slurrycomprises only particles of <10 μm and is spray-dried without difficulty(T_(in)=148° C.; T_(out)=102° C.; 200 Pa below atmospheric pressure).The product granules, which have a residual moisture content of <1% byweight, have an 8″ value of ≦20 in the sedimentation measurementapparatus according to Lorenz (DIN 55992) and produce excellent resultsin high-density polyethylene.

EXAMPLE 2

The procedure is analogous to Example 1 but uses an aqueous presscake ofC.I. Pigment Red 254 instead of Pigment Red 144. The pH value isadjusted to 5.5 using acetic acid. The homogeneous slurry has a measuredaverage particle size of about 1.1 μm, with a specific surface area ofapproximately 10 m²/g, and is spray-dried without difficulty(T_(in)=220° C.; T_(out)=104° C.; 200 Pa below atmospheric pressure).The granules are similarly dust-free, the results in polyethylene beinganalogous to Example 1.

EXAMPLE 3

The procedure is analogous to Example 1 but uses an aqueous presscake ofC.I. Pigment Orange 64 instead of Pigment Red 144 and 294 instead of 189parts by weight of water. A viscosity of from 50 to 850 mPa·s isachieved at a shear rate of from 5 to 500 sec¹. The homogeneous slurryhas a measured average particle size of about 0.80 μm, with a specificsurface area of approximately 12 m²/g, and is spray-dried withoutdifficulty (T_(in)=210° C.; T_(out)=105° C.; 200 Pa below atmosphericpressure). The granules are similarly dust-free, the results inpolyethylene being analogous to Example 1.

EXAMPLE 4

The procedure is analogous to Example 1 but uses an aqueous presscake ofC.I. Pigment Yellow 110 instead of Pigment Red 144 and omits theaddition of water. The pH value is adjusted to 5.8 using formic acid. Aviscosity of from 10 to 30 mPa·s is achieved at a shear rate of from 5to 500 sec⁻¹. The homogeneous slurry has a measured average particlesize of about 10 μm, with a specific surface area of approximately 10m²/g, and is spray-dried without difficulty (T_(in)=180° C.;T_(out)=103° C.; 200 Pa below atmospheric pressure). The granules aresimilarly dust-free, the results in polyethylene being analogous toExample 1.

EXAMPLES 5-6

Example 1 is repeated, but using, respectively, Metolose SM-15™ and 540parts by weight of water, and Metolose SM-1500™ and 108 parts by weightof water (methyl celluloses of about the same methoxy content but ofdifferent viscosity). Comparable results are obtained.

EXAMPLES 7-8

Example 1 is repeated, but using, respectively, Metolose 90SH-100™ and218 parts by weight of water, and Metolose 90SH-4000SR™ and 511 parts byweight of water (hydroxypropyl methyl celluloses having a methoxycontent of about 23-24% and hydroxypropoxy contents of about 5-6% and8-9%, respectively). Comparable results are obtained.

EXAMPLE 9

Example 1 is repeated, but using Pharmacoat 603™ (ShinEtsu,hydroxypropyl methyl cellulose having a methoxy content of about 29-30%and a hydroxypropoxy content of about 8-9%) and 218 parts by weight ofwater. Comparable results are obtained.

EXAMPLE 10

Example 1 is repeated, but using Pharmacoat 904™ (ShinEtsu,hydroxypropyl methyl cellulose having a methoxy content of about 23-24%and a hydroxypropoxy content of about 5-6%) and no additional water.Comparable results are obtained.

EXAMPLES 11-13

Example 1 is repeated, but using, respectively, L-HPC LH-11™ and 168parts by weight of water, L-HPC LH-21 ™ and 101 parts by weight ofwater, and L-HPC LH-31™ and 111 parts by weight of water (ShinEtsu,low-substituted hydroxypropyl celluloses having a hydroxypropoxy contentof about 10-11%). Comparable results are obtained.

EXAMPLES 14-40

Examples 2-4 are repeated, but using the modified celluloses accordingto Examples 5-13 and appropriately modifying the amount of water.

EXAMPLES 41-80

Examples 1-40 are repeated, but using Armeen T™ instead of Armeen TD™.

1. A composition comprising from 92 to 97% by weight organic pigment andfrom 3 to 8% by weight binder, in each case based on the composition,wherein the binder is a mixture consisting of from 5 to 60% by weight,based on the binder, of modified cellulose wherein, on average, perglucose unit, from 0.5 to 1.4 hydroxyl hydrogen atoms are replaced byR₁, or from 0.25 to 0.6 hydroxyl hydrogen atoms are replaced by R₂, orfrom 0.5 to 1.4 hydroxyl hydrogen atoms are replaced by R₁ and from 0 to0.6 hydroxyl hydrogen atoms are replaced by R₂; and from 40 to 95% byweight, based on the binder, of a compound of formula

and from 0 to 20% by weight of further substances; wherein Q is ahydrocarbon radical containing from 12 to 24 carbon atoms, unsubstitutedor mono- to tri-substituted by hydroxy or OR₁, each R₁, independently ofany other R₁, is unsubstituted C₁-C₄alkyl or unsubstitutedC₁-C₄alkylcarbonyl, each R₂, independently of any other R₂, is anorganic group different from R₁ and consisting of 2 to 10 carbon, from 0to 4 oxygen and from 0 to 2 nitrogen atoms, and R₃ and R₄ are eachindependently of the other hydrogen, R₁, R₂, C₅-C₈alkyl,C₅-C₈alkylcarbonyl, C₅-C₈alkenyl, C₅-C₈alkenylcarbonyl, C₅-C₈cycloalkyl,C₅-C₈cycloalkylcarbonyl, C₅-C₈cycloalkenyl, C₅-C₈cycloalkenylcarbonyl,phenyl, benzoyl, tolyl, methylbenzoyl, benzyl, phenylacetyl, phenethylor styryl.
 2. A composition according to claim 1, wherein R₁ is methylor ethyl, R₂ is benzyl, C₁-C₄alkylene-COOR₃, C₂, C₃-alkylene-NR₃R₄ or[C₂-C₃alkylene-O]₁₋₂-H, R₃ and/or R₄ are hydrogen, methyl or ethyl.
 3. Acomposition according to claim 1, wherein the binder comprises from 0 to20% by weight of an organic acid which has from 1 to 8 carbon atoms andis unsubstituted or substituted by hydroxy.
 4. A composition accordingto claim 1, wherein the pigment is selected from the1-aminoanthraquinone, anthanthrone, anthrapyrimidine, azo, azomethine,quinacridone, quinacridonequinone, quinophthalone, dioxazine,diketopyrrolopyrrole, flavanthrone, indanthrone, isoindoline,isoindolinone, isoviolanthrone, perinone, perylene, phthalocyanine,pyranthrone and thioindigo series.
 5. A method of pigmenting apolyolefin or a polyolefin copolymer, wherein from 0.01 to 230% byweight, based on the polyolefin or polyolefin copolymer, of acomposition according to claim 1 is incorporated in a polyolefin orpolyolefin copolymer.
 6. A method of preparing a composition accordingto claim 1, wherein an aqueous medium, an organic pigment, and a binderconsisting of from 5 to 60% by weight, based on the binder, of modifiedcellulose wherein, on average, per glucose unit, from 0.5 to 1.4hydroxyl hydrogen atoms are replaced by R₁, or from 0.25 to 0.6 hydroxylhydrogen atoms are replaced by R₂, or from 0.5 to 1.4 hydroxyl hydrogenatoms are replaced by R₁ and from 0 to 0.6 hydroxyl hydrogen atoms arereplaced by R₂; and from 40 to 95% by weight, based on the binder, of acompound of formula

and from 0 to 20% by weight of further substances; wherein Q is ahydrocarbon radical containing from 12 to 24 carbon atoms, unsubstitutedor mono- to tri-substituted by hydroxy or OR₁, each R₁, independently ofany other R₁, is unsubstituted C₁-C₄alkyl or unsubstitutedC₁-C₄alkylcarbonyl, each R₂, independently of any other R₂, is anorganic group different from R₁ and consisting of 2 to 10 carbon, from 0to 4 oxygen and from 0 to 2 nitrogen atoms, and. R₃ and R₄ are eachindependently of the other hydrogen, R₁, R₂, C₅-C₈alkyl,C₅-C₈alkylcarbonyl, C₅-C₈alkenyl, C₅-C₈alkenylcarbonyl, C₅-C₈cycloalkyl,C₅-C₈cycloalkylcarbonyl, C₅-C₈cycloalkenyl, C₅-C₈cycloalkenylcarbonyl,phenyl, benzoyl, tolyl, methylbenzoyl, benzyl, phenylacetyl, phenethylor styryl, and wherein the weight ratio of pigment to binder is from92:8 to 97:3 and the weight ratio of pigment to aqueous medium is from1:1.5 to 1:100, are successively or simultaneously added to an apparatuswhich is so operated that there results an aqueous dispersion having apH value of from 4 to 7, and the aqueous medium is subsequently removed.7. A method according to claim 6, wherein the pigment is added to theapparatus in the form of a moist pigment cake.
 8. A method according toclaim 6, wherein the aqueous medium is removed by spray-drying.
 9. Amethod of pigmenting organic material, wherein a composition accordingto claim 1 is incorporated in an organic material of natural orsynthetic origin having a molecular weight in the range from 10³ to 10⁸g/mol.
 10. A composition according to claim 1, wherein the pigment isselected from the quinacridone, dioxazine, perylene,diketopyrrolopyrrole and disazo condensation pigment series.
 11. Acomposition according to claim 3, wherein the pigment is from the1-aminoanthraquinone, anthanthrone, anthrapyrimidine, azo, azomethine,quinacridone, quinacridonequinone, quinophthalone, dioxazine,diketopyrrolopyrrole, flavanthrone, indanthrone, isoindoline,isoindolinone, isoviolanthrone, perinone, perylene, phthalocyanine,pyranthrone or thioindigo series.
 12. A method of pigmenting apolyolefin or a polyolefin copolymer, wherein from 0.01 to 230% byweight, based on the polyolefin or polyolefin copolymer, of acomposition according to claim 3 is incorporated in a polyolefin orpolyolefin copolymer.
 13. A method of pigmenting a polyolefin or apolyolefin copolymer, wherein from 0.01 to 230% by weight, based on thepolyolefin or polyolefin copolymer, of a composition according to claim4 is incorporated in a polyolefin or polyolefin copolymer.
 14. A methodof pigmenting a polyolefin or a polyolefin copolymer, wherein from 0.05to 5% by weight, based on the polyolefin or polyolefin copolymer, of acomposition according to claim 1 is incorporated in a polyolefin orpolyolefin copolymer.
 15. A method of pigmenting a polyolefin or apolyolefin copolymer, wherein from 0.05 to 5% by weight, based on thepolyolefin or polyolefin copolymer, of a composition according to claim3 is incorporated in a polyolefin or polyolefin copolymer.
 16. A methodof pigmenting a polyolefin or a polyolefin copolymer, wherein from 0.05to 5% by weight, based on the polyolefin or polyolefin copolymer, of acomposition according to claim 4 is incorporated in a polyolefin orpolyolefin copolymer.
 17. A method according to claim 6, wherein thepigment is selected from the 1-aminoanthraquinone, anthanthrone,anthrapyrimidine, azo, azomethine, quinacridone, quinacridonequinone,quinophthalone, dioxazine, diketopyrrolopyrrole, flavanthrone,indanthrone, isoindoline, isoindolinone, isoviolanthrone, perinone,perylene, phthalocyanine, pyranthrone and thioindigo series.
 18. Amethod according to claim 6, wherein the weight ratio of pigment toaqueous medium is from 1:2.5 to 1:10.
 19. A method according to claim 6,wherein there results an aqueous dispersion having a pH value of from4.5 to 6.5.